> 20+ years ago, software was so horrible that we were just tolerating it,

Absolutely not, especially not on an Apple thread.

By example, the iPod released in 2001. Anyone who used those early knows the user experience was competitive with the current experience. In 2006, I was using the version of iTunes then which was probably objectively the best desktop music app ever created. There are features then that were just there, that were pioneered, or now absent, like an automatically sorted "least listened to" playlist that are now nearly impossible to find. Sync alone is still an headache the OS community just does on the side, and no one is even bothering to compete on it anymore.

I was using (and writing) software as long as 35+ years ago and I disagree with your assessment that we were “just tolerating it” 20 years ago. 20 years ago, I was using Mac OS X Tiger on a new Intel-based MacBook Pro and it ran like a dream, and had software which mostly followed Apple’s human interface guidelines. Now I run macOS Tahoe and curse under my breath at the lack of design consistency and the iPad-ification of the interface. I’m also shown ads, and in some cases ads that can’t be dismissed or disabled, for things like iCloud and Apple Music.

When it comes to the software, I’d take the Tiger experience over the Tahoe one hands-down.